868-84-8

Basic information

• Product Name: S,S'-Dimethyl dithiocarbonate
• Synonyms: S S-DIMETHYL DITHIOCARBONATE;S,S'-DIMETHYL DITHIOCARBONATE;Dimethyldithiocarboxylicacid;dithiocarbonicaciddiethylester;CARBONODITHIOIC ACID S,S-DIMETHYL ESTER;DITHIOCARBONIC ACID S,S'-DIMETHYL ESTER;DIMETHYLDITHIO CARBONATE;Dimethyl dithiocarboxylate
• CAS NO: 868-84-8
• Molecular Formula: C₃H₆OS₂
• Molecular Weight: 122.21
• Product Categories: Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry
• Mol File: 868-84-8.mol
• Article Data: 23

Chemical Properties

• Melting Point: 133-135 °C
• Boiling Point: 169°C
• Flash Point: 144 °F
• Appearance: /
• Density: 1.1705 g/mL at 25 °C
• Vapor Pressure: 3.15mmHg at 25°C
• Refractive Index: n20/D 1.5485
• CAS DataBase Reference: S,S'-Dimethyl dithiocarbonate(CAS DataBase Reference)
• NIST Chemistry Reference: S,S'-Dimethyl dithiocarbonate(868-84-8)
• EPA Substance Registry System: S,S'-Dimethyl dithiocarbonate(868-84-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26-36/37/39
• RIDADR: UN 3334
• WGK Germany: 1
• Hazardous Substances Data: 868-84-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C3H6OS2/c1-5-3(4)6-2/h1-2H3

Synthetic route

methyl O-methyldithiocarbonate (19708-81-7) → S,S-dimethyl dithiocarbonate (868-84-8)

Conditions	Yield
trifluoroacetic acid Ambient temperature;	99%
pyridine N-oxide In neat (no solvent) at 65℃; for 5h;	96%
Aliquat 336 for 1.5h;	90%

S-methyl-O-methyl monothiocarbonate (38103-95-6) + trimethylaluminum (75-24-1) → S,S-dimethyl dithiocarbonate (868-84-8)

Conditions	Yield
Stage #1: trimethylaluminum With sulfur In toluene for 2h; Reflux; Stage #2: S-methyl-O-methyl monothiocarbonate In dichloromethane; toluene at 0 - 20℃; for 2h;	97%

N,N-dimethyl-1-naphthalenamine (86-56-6) + tris-methylsulfanyl-methane sulfuric acid monomethyl ester salt (116538-66-0) → S,S-dimethyl dithiocarbonate (868-84-8) + tetrathioorthocarbonic acid tetramethyl ester (6156-25-8) + 1-Dimethylamino-4-naphthalene (116538-60-4)

Conditions	Yield
With pyridine In acetonitrile for 1h; Ambient temperature;	A n/a B 39% C 86%

tris-methylsulfanyl-methane sulfuric acid monomethyl ester salt (116538-66-0) → S,S-dimethyl dithiocarbonate (868-84-8) + tetrathioorthocarbonic acid tetramethyl ester (6156-25-8) + 1-Dimethylamino-4-naphthalene (116538-60-4)

Conditions	Yield
With pyridine; N,N-dimethyl-1-naphthalenamine In acetonitrile for 1h; Ambient temperature;	A n/a B 39% C 86%

methyl O-methyldithiocarbonate (19708-81-7) + diethylamine (109-89-7) → S,S-dimethyl dithiocarbonate (868-84-8) + S-Methyl N,N-diethylthiocarbamate (37174-63-3)

Conditions	Yield
Stage #1: methyl O-methyldithiocarbonate; diethylamine With triethylamine at 50℃; neat (no solvent); Stage #2: With dimethyl sulfate at 60℃; for 6h; neat (no solvent);	A n/a B 85%

O-Acetyl N-hydroxy-2-thiopyridone (15922-79-9) + Dithiocarbonic acid O-[1-hexyl-2-(toluene-4-sulfonyl)-nonyl] ester S-methyl ester (144432-93-9, 144432-97-3) → S,S-dimethyl dithiocarbonate (868-84-8) + (E)-pentadec-7-ene (16416-37-8) + S-(pyridin-2-yl) 4-methylbenzenesulfonothioate (127878-51-7) + (Z)-pentadec-7-ene (74392-28-2)

Conditions	Yield
In dichloromethane at 40℃; Irradiation; Further byproducts given. Yields of byproduct given;	A 80% B n/a C n/a D n/a
In dichloromethane at 40℃; Irradiation; Further byproducts given. Yields of byproduct given;	A n/a B n/a C 75% D n/a

Dithiocarbonic acid O-[1-hexyl-2-(toluene-4-sulfonyl)-nonyl] ester S-methyl ester (144432-93-9, 144432-97-3) → S,S-dimethyl dithiocarbonate (868-84-8) + (E)-pentadec-7-ene (16416-37-8) + S-(pyridin-2-yl) 4-methylbenzenesulfonothioate (127878-51-7) + (Z)-pentadec-7-ene (74392-28-2)

Conditions	Yield
With O-Acetyl N-hydroxy-2-thiopyridone In dichloromethane at 40℃; Irradiation; Yield given. Further byproducts given. Title compound not separated from byproducts;	A 80% B n/a C 75% D n/a

S,S-dimethylthioacetal of diethyl oxomethanephosphonate (62999-70-6) → S,S-dimethyl dithiocarbonate (868-84-8)

Conditions	Yield
With n-butyllithium; oxygen In tetrahydrofuran at -78℃; 1) 10 min, 2) 15 min;	72%

methyl thiochloroformate (18369-83-0) → S,S-dimethyl dithiocarbonate (868-84-8)

Conditions	Yield
With lithium sulfide In tetrahydrofuran for 2h;	67%

methyl thiochloroformate (18369-83-0) + sodium thiomethoxide (5188-07-8) → S,S-dimethyl dithiocarbonate (868-84-8)

Conditions	Yield
In diethyl ether at 0 - 25℃; for 1h;	61%

methyl O-methyldithiocarbonate (19708-81-7) + methyl iodide (74-88-4) → S,S-dimethyl dithiocarbonate (868-84-8)

Conditions	Yield
at 75 - 110℃; for 140h;	57%

methanol (67-56-1) + dimethyl sulfate (77-78-1) → S,S-dimethyl dithiocarbonate (868-84-8) + methyl O-methyldithiocarbonate (19708-81-7)

Conditions	Yield
Stage #1: methanol; carbon disulfide With potassium hydroxide In diethyl ether; benzene at 6℃; for 5h; Stage #2: dimethyl sulfate In diethyl ether; benzene at 20℃; for 20h;	A 15% B 57%

methyl O-n-propyl dithiocarbonate (25954-88-5) → S,S-dimethyl dithiocarbonate (868-84-8) + S-Methyl-S-(n-propyl) dithiocarbonate (10596-54-0) + S,S-Di(n-propyl) dithiocarbonate (10596-56-2)

Conditions	Yield
4-piperidinylpyridine at 90℃; for 3h; Rearrangement;	A 25% B 45% C 18%
With 3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl 1'-oxide at 80℃; for 8h;	A 22% B 37% C 15%
pyridine N-oxide In dimethylsulfoxide-d6 at 110℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With 4-(dimethylamino)pyridine N-oxide In dimethylsulfoxide-d6 at 80℃; for 6h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
4-piperidinylpyridine at 90℃; for 3h; Title compound not separated from byproducts;	A 25 % Spectr. B 45 % Spectr. C 18 % Spectr.

O-n-butyl S-methyl xanthate (41320-38-1) → S,S-dimethyl dithiocarbonate (868-84-8) + S-(n-Butyl)-S-methyl dithiocarbonate (41320-26-7) + S,S'-di-n-butyl dithiocarbonate (55716-09-1)

Conditions	Yield
4-piperidinylpyridine at 90℃; for 4h; Rearrangement;	A 20% B 38% C 17%
With 3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl 1'-oxide at 80℃; for 8h;	A 21% B 36% C 11%
pyridine N-oxide In neat (no solvent) at 115℃; for 4h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With 4-(dimethylamino)pyridine N-oxide In dimethylsulfoxide-d6 at 80℃; for 6h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
4-piperidinylpyridine at 90℃; for 4h; Title compound not separated from byproducts;	A 20 % Spectr. B 38 % Spectr. C 17 % Spectr.

O-ethyl S-methyl dithiocarbonate (623-54-1) → S,S-dimethyl dithiocarbonate (868-84-8) + S,S-diethyl dithiocarbonate (623-80-3) + S-Ethyl S'-methyl dithiocarbonate (10596-55-1)

Conditions	Yield
4-piperidinylpyridine at 80℃; for 3h; Rearrangement;	A 17% B 17% C 31%
pyridine N-oxide In neat (no solvent) at 90℃; for 7h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With 4-decyloxypyridine N-oxide at 100℃; for 6h; 1.) 100 deg C, 6 h, 2.) heating;	A 30 % Spectr. B 22 % Spectr. C 30 % Spectr.

O-isopropyl S-methyl xanthate (35200-02-3) → S,S-dimethyl dithiocarbonate (868-84-8) + S-Isopropyl S-methyl dithiocarbonate (22426-84-2) + S,S-diisopropyl dithiocarbonate (16118-33-5)

Conditions	Yield
4-piperidinylpyridine at 110℃; for 4h; Rearrangement;	A 18% B 30% C 8%
With 3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl 1'-oxide at 110℃; for 5h;	A 19% B 28% C 6%
pyridine N-oxide In dimethylsulfoxide-d6 at 110℃; for 6h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With 4-(dimethylamino)pyridine N-oxide In dimethylsulfoxide-d6 at 130℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
4-piperidinylpyridine at 110℃; for 4h; Title compound not separated from byproducts;	A 18 % Spectr. B 30 % Spectr. C 8 % Spectr.

methyl O-methyldithiocarbonate (19708-81-7) + triethylamine (121-44-8) → S,S-dimethyl dithiocarbonate (868-84-8) + triethyl(methyl)ammonium S-methyl carbonodithioate (13239-66-2)

Conditions	Yield
at 50℃;	A n/a B 20%
at 45℃; for 2h; neat (no solvent);

<<(methylthio)thiocarbonyl>oxy>cyclohexane (41320-40-5) → S,S-dimethyl dithiocarbonate (868-84-8) + S-Cyclohexyl-S-methyl dithiocarbonate (41320-28-9) + cyclohexene (110-83-8)

Conditions	Yield
4-piperidinylpyridine at 130℃; for 35h; Rearrangement;	A 1% B 12% C n/a

<<(methylthio)thiocarbonyl>oxy>cyclohexane (41320-40-5) → S,S-dimethyl dithiocarbonate (868-84-8) + S-Cyclohexyl-S-methyl dithiocarbonate (41320-28-9) + S,S-dicyclohexyl dithiocarbonate

Conditions	Yield
With 3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl 1'-oxide at 130℃; for 13h;	A 3% B 10% C 2%
With 4-(dimethylamino)pyridine N-oxide In dimethylsulfoxide-d6 at 130℃; for 20h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
1,4-diaza-bicyclo[2.2.2]octane at 150℃; for 4h; Title compound not separated from byproducts;	A 7 % Spectr. B 7 % Spectr. C 7 % Spectr.
1,4-diaza-bicyclo[2.2.2]octane at 150℃; for 4h;	A 7 % Spectr. B 7 % Spectr. C 7 % Spectr.

methyl O-methyldithiocarbonate (19708-81-7) + triethyl(methyl)ammonium S-methyl carbonodithioate (13239-66-2) + diethylamine (109-89-7) → S,S-dimethyl dithiocarbonate (868-84-8) + S-Methyl N,N-diethylthiocarbamate (37174-63-3)

Conditions	Yield
In methanol at 45℃;	A 6% B n/a

<<(methylthio)thiocarbonyl>oxy>cyclohexane (41320-40-5) → S,S-dimethyl dithiocarbonate (868-84-8) + S-Cyclohexyl-S-methyl dithiocarbonate (41320-28-9) + S,S-dicyclohexyl dithiocarbonate + cyclohexene (110-83-8)

Conditions	Yield
With 4-piperidinylpyridine at 150℃; for 11h; Rearrangement;	A 1% B 4% C 2% D n/a

methyl thiocyanate (556-64-9) → S,S-dimethyl dithiocarbonate (868-84-8)

Conditions	Yield
With sulfuric acid

methylthiol (74-93-1) + trichloromethyl ether (20524-84-9) → S,S-dimethyl dithiocarbonate (868-84-8)

Conditions	Yield
at -60℃;

ethyl dithiocarbimidoic acid dimethyl ester (116072-47-0) → S,S-dimethyl dithiocarbonate (868-84-8)

Conditions	Yield
With hydrogenchloride

bis-methanesulfonyl-bis-methylsulfanyl-methane (408309-55-7) → S,S-dimethyl dithiocarbonate (868-84-8)

Conditions	Yield
With sulfuric acid
With water
With hydrogenchloride

O-Acetyl N-hydroxy-2-thiopyridone (15922-79-9) + Dithiocarbonic acid O-(2-benzenesulfonyl-1-hexyl-nonyl) ester S-methyl ester (135581-29-2) → 2-methylsulfanyl-pyridine (18438-38-5) + S,S-dimethyl dithiocarbonate (868-84-8) + (E)-pentadec-7-ene (16416-37-8) + (Z)-pentadec-7-ene (74392-28-2) + S-(pyridin-2-yl) benzenesulfonothioate

Conditions	Yield
In benzene at 25℃; Product distribution; Irradiation; other substrates; other radical initiators; other conditions;

O-Acetyl N-hydroxy-2-thiopyridone (15922-79-9) + Dithiocarbonic acid O-(2-benzenesulfonyl-1-hexyl-nonyl) ester S-methyl ester (135581-29-2) → S,S-dimethyl dithiocarbonate (868-84-8) + (E)-pentadec-7-ene (16416-37-8) + (Z)-pentadec-7-ene (74392-28-2) + S-(pyridin-2-yl) benzenesulfonothioate

Conditions	Yield
In benzene at 25℃; Irradiation; Further byproducts given. Yields of byproduct given;

1-bromo-octane (111-83-1) + potassium methylxanthate (2667-20-1) → S,S-dimethyl dithiocarbonate (868-84-8) + di-n-octyl sulfide (2690-08-6) + dioctyl disulfide (822-27-5) + methyl octyl sulfide (3698-95-1) + S,S-dioctyl dithiocarbonate (69422-58-8) + S-Methyl S-octyl dithiocarbonate (74728-37-3)

Conditions	Yield
Aliquat 336 Product distribution; 1.) room temp., 30 min, 2.) 70 deg C, 2h;

1-bromo-octane (111-83-1) + potassium methylxanthate (2667-20-1) → S,S-dimethyl dithiocarbonate (868-84-8) + dioctyl disulfide (822-27-5) + Octanethiol (111-88-6) + methyl octyl sulfide (3698-95-1) + S,S-dioctyl dithiocarbonate (69422-58-8) + S-Methyl S-octyl dithiocarbonate (74728-37-3)

Conditions	Yield
Aliquat 336 Product distribution; 1.) room temp., 30 min, 2.) 50 deg C, 36h with or without heating the final product mixture;

O-Methyl S-Ethyl Dithiocarbonate (26404-95-5) + O-ethyl S-methyl dithiocarbonate (623-54-1) → S,S-dimethyl dithiocarbonate (868-84-8) + S,S-diethyl dithiocarbonate (623-80-3) + S-Ethyl S'-methyl dithiocarbonate (10596-55-1)

Conditions	Yield
pyridine N-oxide at 110℃; for 4h; Product distribution; Mechanism;

n-octyl methanesulfonate (16156-52-8) + S,S-dimethyl dithiocarbonate (868-84-8) → methyl octyl sulfide (3698-95-1)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide for 0.25h; Heating;	100%

2-chlorobenzo[d][1,3]thiazole (615-20-3) + S,S-dimethyl dithiocarbonate (868-84-8) → 2-methylmercaptobenzothiazole (615-22-5)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide for 0.25h; Heating;	100%

S,S-dimethyl dithiocarbonate (868-84-8) + 1-Chlorooctane (111-85-3) → methyl octyl sulfide (3698-95-1)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide for 0.75h; Heating;	100%

S,S-dimethyl dithiocarbonate (868-84-8) + 1-Iodooctane (629-27-6) → methyl octyl sulfide (3698-95-1)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide for 0.25h; Heating;	100%

S,S-dimethyl dithiocarbonate (868-84-8) + 1-bromo-octane (111-83-1) → methyl octyl sulfide (3698-95-1)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide for 0.25h; Heating;	100%

S,S-dimethyl dithiocarbonate (868-84-8) + 1-octyl p-toluenesulfonate (3386-35-4) → methyl octyl sulfide (3698-95-1)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide for 0.25h; Heating;	100%

S,S-dimethyl dithiocarbonate (868-84-8) + para-chloroacetophenone (99-91-2) → 4-(Methylthio)acetophenone (1778-09-2)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide for 3h; Heating;	100%

S,S-dimethyl dithiocarbonate (868-84-8) + 4-chlorobenzonitrile (100-00-5) → 1-methylthio-4-nitro-benzene (701-57-5)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide for 0.25h; Heating;	100%

S,S-dimethyl dithiocarbonate (868-84-8) + phenylpropyolic acid (637-44-5) → (E)-3-Methylsulfanyl-3-phenyl-acrylic acid (109480-88-8)

Conditions	Yield
With potassium hydroxide at 25 - 60℃; for 0.166667h;	100%

S,S-dimethyl dithiocarbonate (868-84-8) + methylamine (74-89-5) → N-methyl-thiocarbamic acid S-methyl ester (22013-97-4)

Conditions	Yield
In water at 20 - 25℃; for 0.25h;	100%
In water at 20 - 25℃; for 0.25h;	100%
In water at 20 - 25℃; for 0.25h;	100%

S,S-dimethyl dithiocarbonate (868-84-8) + N-butylamine (109-73-9) → S-methyl N-butylthiocarbamate (39078-72-3)

Conditions	Yield
In water at 20 - 25℃; for 2h;	100%
In water at 20 - 25℃; for 2h;	100%
In water at 20 - 25℃; for 2h;	100%

S,S-dimethyl dithiocarbonate (868-84-8) + hexan-1-amine (111-26-2) → S-methyl N-hexylthiocarbamate (120904-15-6)

Conditions	Yield
In water at 20 - 25℃; for 2h;	100%

S,S-dimethyl dithiocarbonate (868-84-8) → urea (57-13-6)

Conditions	Yield
With ammonia; water at 60℃; for 2h;	100%

S,S-dimethyl dithiocarbonate (868-84-8) + C8H6ClNO → C8H9NS

Conditions	Yield
With potassium hydroxide In water	100%

S,S-dimethyl dithiocarbonate (868-84-8) + dimethyl amine (124-40-3) → S-methyl dimethylthiocarbamate (3013-02-3)

Conditions	Yield
In water at 20 - 40℃;	99.5%

S,S-dimethyl dithiocarbonate (868-84-8) + 2-((bis(2-aminobenzyl)amino)methyl)aniline (222638-73-5) → tris[2-(methylthiocarbonylamino)benzyl]amine

Conditions	Yield
Stage #1: 2-((bis(2-aminobenzyl)amino)methyl)aniline With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: S,S-dimethyl dithiocarbonate In tetrahydrofuran; hexane at 20℃; for 6h; Further stages.;	99%

S,S-dimethyl dithiocarbonate (868-84-8) + ethylamine (75-04-7) → S-methyl N-ethylthiocarbamate (39076-43-2)

Conditions	Yield
In water at 20 - 25℃; for 5h;	98.8%
In water at 20 - 25℃; for 2h;	97%
In water at 20 - 25℃; for 2h;	97%

S,S-dimethyl dithiocarbonate (868-84-8) + isobutylamine (78-81-9) → S-methyl N-isobutylthiocarbamate

Conditions	Yield
In water at 20 - 25℃; for 4.5h;	98.6%

S,S-dimethyl dithiocarbonate (868-84-8) + benzylamine (100-46-9) → S-Methyl N-benzyl(thiocarbamate) (90609-83-9)

Conditions	Yield
In water at 20 - 25℃; for 15h;	98%
In water at 20 - 25℃; for 15h;	98%
With n-butyllithium; diisopropylamine 1.) THF, hexane, -78 deg C, 0.5 h, 2.) room temperature, 20 h; Yield given. Multistep reaction;

S,S-dimethyl dithiocarbonate (868-84-8) + 1-aminodecane (2016-57-1) → N,N'-Di-n-decylurea (1943-09-5)

Conditions	Yield
In water at 60℃; for 4h;	98%

S,S-dimethyl dithiocarbonate (868-84-8) + maleic acid (110-16-7) → (+/-)-methylsulfanyl-succinic acid (22119-05-7)

Conditions	Yield
With potassium hydroxide at 90℃; for 2h;	97%

S,S-dimethyl dithiocarbonate (868-84-8) + 1-amino-2-propene (107-11-9) → 1,3-diallylurea (1801-72-5)

Conditions	Yield
In water at 60℃; for 6h;	97%
In methanol at 60℃; for 24h;	80%

S,S-dimethyl dithiocarbonate (868-84-8) + 4-Aminobutanol (13325-10-5) → S-methyl N-(4-hydroxybutyl)thiocarbamate

Conditions	Yield
In water at 20 - 25℃; for 3h;	97%

S,S-dimethyl dithiocarbonate (868-84-8) + ethanolamine (141-43-5) → dimethylenecyclourethane (497-25-6)

Conditions	Yield
In water at 20 - 25℃; for 15h;	97%

S,S-dimethyl dithiocarbonate (868-84-8) + methylamine (74-89-5) → N,N'-Dimethylurea (96-31-1)

Conditions	Yield
In water at 60℃; for 2h;	97%

4-(4-amino-3-fluorophenoxy)pyridine-2-carboxylic acid methyl amide (757251-39-1) + S,S-dimethyl dithiocarbonate (868-84-8) + 4-chloro-3-trifluoromethyl-aniline (320-51-4) → regorafenib (755037-03-7)

Conditions	Yield
With tetra(n-butyl)ammonium hydroxide In tetrahydrofuran at 35℃; for 1.33333h; Green chemistry;	96.2%

S,S-dimethyl dithiocarbonate (868-84-8) + ethylamine (75-04-7) → N,N'-diethylurea (623-76-7)

Conditions	Yield
In water at 60℃; for 5h;	96%
at 100℃;

S,S-dimethyl dithiocarbonate (868-84-8) + isobutylamine (78-81-9) → N,N'-di-isobutylurea (1189-23-7)

Conditions	Yield
In water at 20 - 60℃; for 18h;	96%
In water at 60℃; for 10h;	95%
In methanol at 60℃; for 24h;	92%

Upstream product

• 74-93-1 methylthiol 
• 20524-84-9 trichloromethyl ether 
• 116072-47-0 ethyl dithiocarbimidoic acid dimethyl ester 
• 17659-13-1 Methyl xanthogenic acid benzylester 
• 41320-40-5 <<(methylthio)thiocarbonyl>oxy>cyclohexane 
• 2667-20-1 potassium methylxanthate 
• 100-44-7 benzyl chloride 
• 18369-83-0 methyl thiochloroformate 
• 5188-07-8 sodium thiomethoxide 
• 19708-81-7 methyl O-methyldithiocarbonate 
• 74-88-4 methyl iodide 
• 41320-41-6 O-n-decyl S-methyl dithiocarbonate 
• 73476-32-1 (bis-methylsulfanyl-methylene)-semicarbazide 
• 7732-18-5 water 

Downstream Products

• 623-76-7 N,N'-diethylurea 
• 73067-21-7 S-methyl 2,4,4-trimethyl-6-oxocyclohex-1-ene-1-carbothioate 
• 73067-22-8 6-Isopropenyl-3-methyl-2-oxo-cyclohex-3-enecarbothioic acid S-methyl ester 
• 41317-80-0 Methanesulfonyl-phenyl-thioacetic acid S-methyl ester 
• 41317-78-6 Benzenesulfonyl-phenyl-thioacetic acid S-methyl ester 
• 41317-81-1 Phenyl-phenylmethanesulfonyl-thioacetic acid S-methyl ester 
• 73067-19-3 2-methyl-6-(methylthiocarbonyl)cyclohexanone 
• 16630-65-2 S-methyl-3-mercaptobutyric acid 
• 3698-95-1 methyl octyl sulfide 
• 62574-23-6 2-methyl-3-methylsulfanyl-propionic acid 
• 124-63-0 methanesulfonyl chloride 
• 107427-80-5 S-methyl cyano(phenyl)thioacetate 
• 646-01-5 3-(methylsulfanyl)propionic acid 
• 109480-88-8 (E)-3-Methylsulfanyl-3-phenyl-acrylic acid 

Relevant articles and documents

Trifluoroacetic Acid Catalysed Rearrangement of Dialkyl Xanthates to Dithiocarbonates with Inversion of Configuration

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Identification and biosynthesis of tropone derivatives and sulfur volatiles produced by bacteria of the marine Roseobacter clade

Bacteria of the Roseobacter clade are abundant marine bacteria and are important contributors to the global sulfur cycle. The volatiles produced by two of its members, Phaeobacter gallaeciensis and Oceanibulbus indolifex, were analyzed to investigate whether the released compounds are derived from sulfur metabolism, and which biosynthetic pathways are involved in their formation. Both bacteria emitted different sulfides and thioesters, including new natural compounds such as 5-methyl phenylethanethioate (16) and butyl methanesulfonate (21). The S-methyl alkanoates were identified by comparison with standards that were synthesized from the respective methyl alkanoates by a new method using an easily prepared aluminium/sulfur reagent. Phaeobacter gallaeciensis is also able to produce tropone (37) in large amounts. Its biosynthesis was investigated by various feeding experiments, showing that 37 is formed via a deviation of the phenylacetate catabolism. The unstable tropone hydrate 42 was identified as an intermediate of the tropone biosynthesis that was also released together with tropolone (38). The Royal Society of Chemistry 2010.

O,S-Dimethyl carbonodithioate as a phosgene substitute for the preparation of S-methyl alkylcarbamothioates and dialkylcarbamothioates

O,S-Dimethyl carbonodithioate is proposed as a suitable and safely handled reagent that can be used as a replacement for phosgene in the synthesis of S-methyl alkyl- and dialkylcarbamothioates. The former were obtained by a two-step procedure, which can also be carried out in a one-pot fashion without isolating the intermediates O-methyl alkylcarbamothioates; the overall yields of the pure S-methyl alkylcarbamothioates were 94-98%. Optimal conditions for the synthesis of S-methyl dialkylcarbamothioates involved a one-step procedure in a solvent-free system in the presence of triethyl(methyl)ammonium methyl carbonate as a catalyst; yields of the pure products were 85-98%. A mechanism is proposed for the carbamothioate-formation reaction. Georg Thieme Verlag Stuttgart.